How to create a compelling travel contest or giveaway

I used to think it was Hocus Pocus when brands were offering big-ticket prizes like extravagant trips or doing a contest to score the ‘World’s Best Job’ which included traveling the world as their resident blogger-in-chief. That is until I became that brand and agency behind them. When working for tourism brands, publicists conjure up these grand giveaways and buzz-worthy incentives for several reasons, which we’ll dive into soon. It’s another tool in our public relations/marketing toolkit for our brands to remain top of mind. 

When creating a contest, companies put considerable thought into what would motivate people to enter, the call to action(s), and what their end goals are. We aren’t throwing cash into the wind to see what sticks. We aim to gain consumer interest, capture email contacts, expand our market share and get into the headlines. 

Increasing awareness and creating compelling content to engage prospective clients is key. Before jumping headfirst into your first giveaway, there are a lot of things to consider, and it’s imperative to remain compliant with legal restrictions. After years of doing these with all prize types, big and small, I’ve decided to share my tips and tap other top experts to share their insight on the topic of travel contests and giveaways…

Value Proposition and Goals 

Before you start conceptualizing the contest, consider your value proposition and how to highlight your brand’s strengths or news (this could be a new offering or service, for example) through this campaign. If you’re a hotel chain, you will want to create an opportunity to talk about what sets you apart from your competition. Are you a destination? Showcase your activities, dining scene, or local partners. If you’re a travel advisor association, you want to show off a travel agent's value and travel planning prowess. Weave those features into the giveaway value. 

If you are an airline launching a new route, you may want to consider giving tickets on that new route plus a hotel or tour to complete the prize. Get creative. Think about other partnerships that would be mutually beneficial and help expand your reach. Lori Dennis, Customer Marketing at Scott’s Cheap Flights has had a lot of experience working with airline partners. “We’ve had great success partnering with small airlines who are looking to reach new audiences and promote new flight routes. For example, we partnered with value-driven airline French bee when they introduced new routes from Los Angeles to Paris and Tahiti late last year,” said Lori.

It is crucial that you zero in on your target audience and goals with key decision-makers.  Are you trying to grow your email list with opt-ins? Gain new social media followers and on which platform(s)? Do you want content to reshare? Are you trying to gain awareness? Are you trying to foster relationships with content creators? Are you trying to get media coverage? Don’t check all of the above or you’re in for a complicated ride. Remain realistic with the ROI, so you can be happy when you exceed expectations when done right. 

Build your prize around the goals. Create balance with the carrot and call to action(s). Consumers are more reluctant to give their emails these days; content creators are being asked too many times to work for free, and some things are just too gimmicky to share. Put yourselves in the shoes of those groups you’re aiming to reach. Free travel with lots of strings attached isn’t as big of an incentive as it used to be. 

With the technology we have today, there are plenty of ways to check a few boxes and tailor the giveaways. Lori shared, “the call to action(s) will vary depending on your goals, but for Scott’s Cheap Flights, we typically run giveaways when we’re looking to create a spike in referral behavior. This tactic will obviously only work if you have a referral program in place and a product or service that lends itself to referrals, but there are so many other ways to incentivize action. One thing I love about giveaways is that they are highly customizable and can really help your organization achieve a specific goal, whether you’re trying to hit a target number of signups, social media followers, or email addresses for retargeting.” 

Appeal to special interests and create irresistible content. For example, anything that includes showing off our pups or pets will be a surefire winner, because people love their fur babies. Just look at AvantStay with their recent Dog Casting Call that clearly was a winner and garnered them inclusion in a Forbes article by Ramsey Qubein. “I find that travel contests do generate buzz,” said Ramsey. Keep an eye on his column for more. Another place to find curated lists of travel giveaways (or to pitch) is JohnnyJet’s newsletter

My cute pups for reference of dog mom love.

Working with a Strategic Partner 

Bringing on partners can be a great way to increase your reach and giveaway value. Be smart about those you do bring on that align with your brand. Make sure each brand team commits to the terms and marketing program. I can’t tell you how many times this can fall through the cracks or you find yourself playing hot potato regarding responsibilities. You need to be as clear with the partners as you will with the legal terms that we’ll get to shortly. 

Outline things like ‘where does the campaign live — a website specifically for this giveaway or on a partner backpage, who’s covering the creative design with brand guidelines, who’s handling the terms & conditions, and overall project timeline with deliverables aka a project manager.’ 

DojoMojo & Wine Awesomeness partnership promo

You may want to consider platforms that take a lot of the hard work out of the equation by finding others that are interested in giveaways, and co-marketing partnerships like DojoMojo, which was founded by a dear friend Logan Lee at Wine Awesomeness. 

From the day I met Logan, he was a big email growth proponent, so much so that we would all shout ‘take a drink’ every time he said the word email. It was a dangerous game, but boy was he right about building solid email databases. We hosted many campaigns for my clients, and the platform included notable outlet partners like Hearst, Condé Nast, Matador Network, and email influencers like TheSkimm. Logan saw a need in the market and made a customizable solution that took care of the heavy lifting. 

Why would an influencer, writer, or creator enter? 

Everyone wants more eyeballs, more publicity, and more more more. It’s just the nature of expectations these days. Do more with less. But, you also need to be good contest stewards or it will come back to bite you with unwanted chatter, bad consumer sentiment, and brand damage. The travel industry is a small place and people love to talk. 

Back in 2018, The New York Times broke the travel industry internet with its ‘job listing’ for The 52 Places Traveler. In a story following the selection process, the article said, “they received over 13,000 applications for our first-of-its-kind job: a traveler who will go to each and every place on this year’s Places to Go list.” 

After giving it some thought about applying myself, 52 destinations, 52 weeks in the year, sounded like a tall order to not only visit but ALSO to do reporting. It was clear it was for serious journalists only who would want to get in front of The Times staff. There was potential to work with them after the project and be able to put that feather in your cap for giving it a go too. They ultimately went with a seasoned travel writer who still writes for the publication. 

Most recently,  the biggest headline-grabbing contest award goes to Marriott’s TikTok 30 Stays in 300 Days. It was covered by many major outlets, shared among all the travel Facebook groups, and so on. Marriott posted, “In your submission, Marriott Bonvoy wants to see your distinct perspective on travel and what you’ll bring to their TikTok channel.” The stipulations were to 1) Follow @MarriottBonvoy on TikTok. 2) Create a TikTok to explain why you should be one of the three Marriott Bonvoy TikTok Correspondents. 3) Include the hashtags #30stays300days and #contest. 

Alle Pierce, an amazing content creator and travel advisor at AlleAbroad.com, entered the Marriott TikTok contest this year because it had several attractive components for her. She said, “With those contests, I know it's a long shot, however, it's worth it to shoot my shot just to see, since I have a flexible schedule and it could be an excellent opportunity to see the world through these properties. It’s a potential chance to work with Marriott on several of my business aspects like Gals Abroad Getaways, or experience the properties to share with my clients and community.” 

As travel advisors, we do need to experience many properties first-hand to be able to recommend them to our clients. That kind of investment that goes into being a travel expert can be enticing through this particular contest type. 

PRO Tip: There are various reasons to enter, and the incentives need to match the amount of work and reward. 

“One of those bucket list opportunities when you get flown out on someone else's dime in a completely unique shared experience with others,” can be worth the time developing video for someone like Alle who can do it in her sleep. 

Another buzz-worthy example is Bumble’s search for a ‘Global Connector Bee’ in which they chose two ladies to travel together if you get selected. Ultimately, they chose someone who I had worked with and knew well, Juliana Broste, aka Traveling Jules who explains more here. However, the pandemic shut that fun adventure down. When you make these contests, make sure to come up with a contingency plan, since the pandemic has taught us anything can happen. 

Years ago, there was a contest that set off a ton of imitators in its wake: The “Best Job in the World” by Queensland. Angie Orth, a former travel PR colleague, content creator at AngieAway, and a finalist for that contest said, “I can’t tell you how many of my past and current PR consulting clients ask about how to do the next Best Job campaign!” Now, everyone is trying to “recreate that lightning in a bottle,” she says. 

I definitely agree. It matters the level of budget you have to work with and the notoriety of your brand and collaborators. 52 Places had the luxury of being a prominent media outlet with a built-in audience, and Marriott is a global brand so the TikTok juggernaut was able to capture that magic. 

Angie notes, “what a brilliant campaign, Tourism Queensland! They ultimately populated YouTube with 34,000 60-second commercials about Australia/Queensland/The Great Barrier Reef and then had 50 rabid finalists doing free PR around the world for them for months. For about $1 million, they generated over $200 million in publicity. Diabolical and absolutely genius!” Read all about it on her site, and why it’s important to not ask people to work for free

That’s why if you’re looking for professional content creators to participate, you need to be transparent. Don’t bog the submission down with many requirements. 

If you’re a smaller brand or don’t have a Marriott budget, you can organize effective email giveaways and gradually work your way up. See how people react and keep modifying, always with the value proposition front and center. 

If you’re selecting from the general public and not ‘professional creators’ like the Vacation Do Over by the American Society of Travel Advisors (ASTA), be cognizant that they are not actors or professionals in this space. They have less flexible jobs to participate in your campaign if you want them to follow a timeline and create content. Build in support and ways to coach them, but don’t expect to control the outcome. 

We’ve probably all had a vacation that was an absolute blunder that you wish you could do over. With a trip valued at $10,000 plus a travel expert planning it all for you, the trip giveaway drove tons of organic media hits, tons of entries, and extensions to the campaign. The submission did require a video submission, so be mindful of the portal to entry, less tech-savvy individuals, and huge file sizes. You are going to get more raw entries and that tends to resonate with others. *Disclosure: I worked closely on this project, which is why I know so much! 

Pay-for-Play Participation 

Don’t hope and pray your giveaway will get picked up in the news and power your entries; pay-for-play where you need to in order to get the guaranteed audience and distribution you want. That’s why partners can be extremely helpful and the prize needs to be worthwhile. 

You cannot plan to have a viral campaign. You can create the right environment, and pay influencers that would be open to working with you to get the word out. If you’re trying to get submissions on TikTok, get TikTok influencers. If you want Facebook, look for someone with a good following on that platform, and so on with email database strength. 

Project Timeline & Project Lead 

With all these things to remember and deliverables, you must create a work-back plan, and assign a detail-oriented project manager. When do you actually want to announce, when/how do you want to pick your winner and when do you want to execute the redemption or prize deliverables? Do you want to do a press release or pitch this to targeted media? 

Stay on top of the due dates and winner experience. It’s not only about the flash. It’s about how each interaction with your brand is a positive one, even when it includes offering prizes. The campaign does need to be handled well. 

“My other favorite thing about giveaways is contacting the winners. It’s one of my favorite parts of my job!,” shared Lori. That is actually the fun part when you get to make someone’s day and tell them they’ve won. Remember to publicly announce your winner (or several) so people know the process was followed, and they’re not waiting for feedback if they won – especially if this was a bigger submission effort. 

Staying Compliant: Terms & Conditions

We may be tackling T&Cs last in this post, but by no means, is it the least important component. You can never start too early bringing in legal to the planning and creation phase. Remember that time Oprah gave away free cars to the whole audience and turned out, it cost everyone thousands in taxes? Yeah, don’t be that guy. You get a vacation, you get a tax-free vacation. 

Some common terms to consider:

  • In many cases when it’s travel, most companies will allow entrants in the continental US - leaving out Hawaii, Alaska, and other US territories. 

  • Brands will also want to implement blackout dates on peak travel dates, and flexible travel redemption – given Covid or life circumstances. Outline in the terms the companies involved so there are no conflicts of interest and exclude friends and family connected to the companies hosting the contest. 

  • Follow your own rules, especially that the finalists followed your requirements, and don’t be caught playing favorites.

With that in mind, I reached out to my legal consultant to help shed light on some of the legal implications of a travel contest or giveaway.  who runs a full-service shop and great counsel for this topic. Nuzayra Haque-Shah, attorney and founder of NH Legal, shares her opinion below. **This is not legal advice but only intended to be general information. Please consult an attorney for legal advice specific to your needs

What are the toughest contests or most complex to create terms & conditions? 

– The most complex ones are where the contest creator is not clear about the process and desired outcome. For example, if you give vague instructions on the geographical territories where the contest will run or the method of selecting the winners – it makes it very hard to draft good Terms and Conditions. This is because the laws that will apply, the safeguards that need to be put in place, and the overall format of the Terms & Conditions become too broad trying to encompass a lot of scenarios that may not be relevant for this particular contest.

Do you have to keep a giveaway under a certain monetary value or recommend (due to bonding and registering)? Does a winner have to pay taxes or file paperwork after? 

– Every US state has its own contest laws so it's important as a contest creator to consult with an attorney in your state for any applicable limits.

–As a contest winner, yes generally you have to declare winning a monetary prize on your taxes, similar to winning the lottery. For example, if you receive travel credit and gift cards for creating content for a hotel chain – you would have to account for all that as compensation for your services. Also, under federal law contest winners are required to pay taxes on prizes they win, if the prizes are over $600.

What are things you should avoid in giveaways? 

– In any giveaway or contest do not ask people to purchase to take part in the contest. It's illegal.

– If someone wins a physical product, don’t ask them to pay high shipping and delivery fees.

– Be careful about children, some states restrict the type of advertisements you can place in front of children

– If you want content submission as part of a contest, clarify who owns the intellectual property rights to the content and how the rights will be handled. For example, do you want the creator to retain the rights and give you a license to use the content or otherwise?

– For content submission, state that the content submitted must be original and not taken from a third party as you could be held liable for intellectual property infringement

Do you have any suggestions for a timeline – when to reach out to someone like yourself & team for legal preparation or how early to start? 

– As soon as you can. As an influencer or content creator taking part in contests, creating content for brands, or endorsing any brand products – there are regulations you have to follow otherwise there could be penalties. Also, it's important to have an attorney review your contract before you sign it – to make sure that the contract is favorable to you and that you are not taking on unintended liability. Remember that when attorneys prepare contracts they do so with their client's best interests in mind. Contracts are not meant to be inherently fair – its meant to benefit the party preparing it so you need an attorney on your side to look out for you.

 Similarly, for brands wanting to run contests you have to talk to an attorney from the point of conception of the idea, so your attorney can advise you about the legalities and also help you with creating Terms and Conditions that make the contest fun for the participants and lucrative for your business.

What is the average cost or average to create proper legal terms? 

– I can't comment about other law firms but with my practice, we do everything at a flat fee so the client knows exactly what the investment is and there's no surprise invoice at the end of the month. We have fillable ready-to-use templates at $550 and customization starts at $1500 and can go up to $3,500 depending on the complexity of the Terms and Conditions. 


For more information and consulting, reach out to Trip Whisperer agency, enlist the legal counsel of NH Legal, leverage a platform, or partner with existing services, and keep in mind that there’s no such thing as a silver bullet.

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